Sodium hydride → methyl 7-nitro-2,3-dihydro-1H-pyrrolo[1,2-a]indole-8-carboxylate

HRID 715956Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 715956
[H-].[Na+].CS(O[CH2:8][CH2:9][CH2:10][C:11]1[NH:12][C:13]2[CH:14]=[CH:15][C:16]([N+:24]([O-:26])=[O:25])=[C:17]([C:20]([O:22][CH3:23])=[O:21])[C:18]=2[CH:19]=1)(=O)=O>CN(C=O)C.C(OCC)(=O)C>[N+:24]([C:16]1[CH:15]=[CH:14][C:13]2[N:12]3[CH2:8][CH2:9][CH2:10][C:11]3=[CH:19][C:18]=2[C:17]=1[C:20]([O:22][CH3:23])=[O:21])([O-:26])=[O:25]

Komponenten

5

Edukt 2

HCID 24758Sodium hydrideHCID 86712115methyl 2-(3-methanesulfonyloxypropyl)-5-nitro-1H-indole-4-carboxylate2×

Produkt 1

HCID 70984130methyl 7-nitro-2,3-dihydro-1H-pyrrolo[1,2-a]indole-8-carboxylateAusbeute 95,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

Sodium hydride (60% dispersion in oil, 0.096 g) was added to a solution of methyl 2-(3-methanesulfonyloxypropyl)-5-nitro-1H-indole-4-carboxylate (Intermediate 20, 0.460 g) in DMF (12 mL) and the resultant mixture was stirred at room temperature for 30 minutes. The mixture was diluted with ethyl acetate and washed with water and brine, dried (MgSO4) and filtered. The filtrate was concentrated in vacuo to give methyl 7-nitro-2,3-dihydro-1H-pyrrolo[1,2-a]indole-8-carboxylate (0.320 g) as a brown solid.

Aufarbeitung

  1. washwashed with water and brine
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-0213e223de8345aea448f4bfb6dfc373
Quelldatensatz
uspto-grants-2015_11
Patentnummer
US09187494B2

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